The critical incident explores the complexities Jan, owner of JDD Rockway LLC, faced in navigating the challenging U.S. freight market post-COVID-19 pandemic. The focal point of the case is Jan's trilemma in dispatching options: using a third-party dispatching service, hiring an in-house dispatcher, or managing dispatch himself. Each option's financial implications and operational impacts are analyzed, highlighting the choices' advantages and challenges. The article provides insights into Jan's decision-making process amid evolving market conditions and underscores the broader implications for small carriers in the current freight landscape.